5 upcoming free agents playing for a new deal in the NBA Playoffs

4. Khris Middleton

Khris Middleton is going to be one of the more polarizing free agents this off-season if he decides to opt out of the last year of his contract with the Bucks. At age 32, Middleton can opt into the final year of his deal with Milwaukee to make roughly $40 million. But given his age, this could be his last opportunity to secure a long-term contract.

Middleton has been a core member of the Bucks since he was drafted in 2012 and was a key cog in their championship run from two years ago. When the game slows down and the Bucks need a bucket late in the game, they often choose to lean on Khris Middleton over two-time MVP Giannis Antetokounmpo.

The two-way wing is coming off an injury-riddled season in which he only appeared in 33 regular season games. However, he performed just as well this season as he has in the four years prior, three in which he was selected to be an NBA All-Star.

Khris Middleton has become one of the best and most underrated perimeter players in the NBA. The Bucks have been able to maintain their championship core for the most part, but Middleton could put the team at a real crossroads this Summer.

Do they risk losing such an important piece of their team? Or do they give him a hefty long-term extension that keeps him with the Bucks into his mid-to-late 30s? Middleton’s knee injury makes this a tougher decision for both sides.